#1 KEF-BWI Boeing 757-200 TF-FI* April 1998 (3 months old - when I was 6 month old I had flown all aircraft types flying in Iceland excluding the DHC-6 )
#25 Something late 1998 (I was born in Jan 1998 and flew about 30 flights the 1st year)
#50 Sometime in 2004-2006 (2001-2003 when I was 3-5 had few flights as my brother was born in 2001)
#75 LPA-LGW Boeing 757-200 G-BY** April 2007 (With my best friend for 8 years now)
#100 BOS-TPA Airbus 320-200 N591JB Oct 2008 (Going to Florida for the 20th time then - have gone 27 times now )
#125 BOS-KEF Boeing 757-300 TF-FIX Jun 2010 (After an adventurous trip home from Florida with 3 cancellations)
#150 CGN-FCO Airbus 319-100 D-AGWL Jul 2011 (Going to Rome, amazing city!)

Have 154 flights right now after my Florida trip (27th) last October with my best friend and our families.

My number one is quite difficult. I used to fly a lot on MP's 310's and 742's and even DC-10's as a kid, but I don't remember a single thing. I have decided not to count these flights as flown. Instead I use the first flight I actually remember. (Very well I might add)